FR2855172A1 - Broad-spectrum antimicrobial agents, useful e.g. as medicaments, cosmetic agents, plant protectants or preservatives, comprising new or known 3-desoxy-anthocyanidin compounds - Google Patents

Abstract

The use of 3-desoxy-anthocyanidins (i.e. flavylium (or 2-phenyl-1-benzopyrilium) salts) (I) as antimicrobial medicaments, as cosmetic agents, as antimicrobial agents for combating plant diseases, as preservatives or in antimicrobial materials is new. The use of 3-desoxy-anthocyanidins of formula (I) is claimed: (1) in the production of medicaments for treating microbial infections in mammals (especially humans); (2) in the production of cosmetic products; (3) for combating microbial diseases in plants; (4) for preserving perishable products (especially foods); and (5) for preparing antimicrobial materials. [Image] R 1- R 5, R 7- R 11H, halo, OH, NO 2, CN, alkoxy, acyloxy or alkyl (all of 1-12C and optionally unsaturated), a group containing at least one of Si, S and/or P; -O-glycosyl (optionally substituted (os) by alkoxy, acyloxy or alkyl (all of 1-12C and optionally unsaturated)), 2-30C alkenyl or cycloalkenyl (optionally interrupted by heteroatom(s) (specifically O, S or N and os), aryl, aralkyl, alkaryl (all of 6-30C and os), or -NY 1Y 2or -N=CY 1Y 2; Y 1, Y 2H, optionally unsaturated 1-12C alkyl, 2-30C alkenyl or cycloalkenyl (optionally interrupted by heteroatom(s) (specifically O, S or N and os), aryl, aralkyl or alkaryl (all of 6-30C and os); or Y 1+ Y 2group completing an os 4-8 (preferably 5-7) membered, aromatic or non-aromatic ring, preferably formed from C, N, O and/or S atoms; R 6H, halo, NO 2, CN, a group containing at least one of Si, S and/or P, 2-30C alkenyl, cycloalkenyl (optionally interrupted by heteroatom(s) (specifically O, S or N and os), aryl, aralkyl or alkaryl (all of 6-30C and os), or -NY' 1Y' 2, -N=CY' 1Y' 2; Y' 1, Y' 2as for Y 1, Y 2, except that Y' 1+ Y' 2cannot form a ring; two adjacent groups R 1- R 11group completing an os 4-8 (preferably 5-7) membered, aromatic or non-aromatic ring, preferably formed from C, N, O and/or S atoms; X ->anion derived from an organic or mineral acid (especially acetate, borate, citrate, tartrate, bisulfate, sulfate, phosphate, bromide, chloride, tetrafluoroborate or perchlorate) or from a sulfate or sulfonate group. in R 1-R 5, R 7-R 11the alkoxy, acyloxy or alkyl are all of 1-12C and optionally unsaturated; the group containing at least one of Si, S and/or P; -O-glycosyl is optionally substituted by alkoxy, acyloxy or alkyl (all of 1-12C and optionally unsaturated), Independent claims are included for: (a) (I) as new compounds, provided that R 3and R 10are restricted to the values given above for R 6; and (b) the preparation of the new compounds (I). ACTIVITY : Antibacterial; antifungal. 4'-Hydroxy-flavylium chloride (Ia) had minimum inhibitory concentration values of less than 3.0 Microg/ml against Staphylococcus aureus(both sensitive clinical strain IBS211 and methicillin-resistant clinical strain IBS04) and less than 60 Microg/ml against Pseudomonas aeruginosa, Candida albicans(strain IHEM 8060), Candida glabrata(patient strain) and Aspergillus fumigatus(strain GASP 4707). MECHANISM OF ACTION : None given in the source material.

Description

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3-DESOXYANTHOCYANIDINE COMPOUNDS AND THEIR
USES AS ANTIMICROBIAL AGENTS
The present invention relates to the fields of organic chemistry and microbiology. More specifically, the invention is part of the search for chemical compounds having advantageous antimicrobial properties.

 In particular, the present invention relates to 3desoxyanthocyanidin compounds having antibacterial and antifungal properties, especially useful for therapeutic and / or prophylactic, cosmetic, phytosanitary and in the food industry.

 The invention also relates to processes for the preparation of such compounds.

 Anthocyanins, molecules that are part of the flavonoid family and able to absorb visible light, are pigments that color plants in blue, red, mauve, pink or orange. At the origin of the color of the flowers, fruits and berries, they are generally located in the vacuoles of the epidermal cells, which are real pockets filled with water.

 The aglycone of anthocyanin, which is also the chromophore, is called anthocyanidin. Anthocyanins have a common basic structure, the flavylium cation or 2-phenyl-1-benzopyrilium whose positions are described as shown in formula (1) below.

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 It is well established that natural anthocyanins possess a biological activity that has been widely described in the literature.

 Until now, anthocyanins and anthocyanidins have been widely used as natural dyes in textile dyeing (US Patent 3,266,903).

 The use of unsubstituted flavylium compounds at the 3-position and substituted by at least one hydroxyl or alkoxy radical at the 4 'position is also known to those skilled in the art for the following applications: the use as a dyes in compositions for dyeing keratinous fibers and for dyeing the skin, or for the manufacture of such compositions (patent applications FR 2 811 558 and WO 98/27940).

 Similarly, certain flavylium compounds have been described as having anticholestemic activity of interest (US Pat. No. 3,546,250).

 In addition, anthocyanins, that is, flavyliums bearing an oxo group at the 3-position, are known to be phytoalexins, which represent, in a large variety of plant species, an essential mechanism of immune defense against infections. .

 In recent years, strains of gram-positive pathogenic bacteria, such as Staphylococcus, Streptococcus, Mycobacterium and Enterococcus, which are clinically isolated, are increasingly showing resistance patterns and are, therefore, particularly difficult to control.

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 eradicate. By way of example, mention may be made especially of methicillin-resistant Staphylococcus aureus strains (MRSA).

 Thus, in human health, the incidence of opportunistic microbial infections has been steadily increasing in recent years.

For illustration, according to the World Health Organization (WHO), more than 95% of strains of Staphylococcus aureus are resistant to penicillin and more than 60% of them have also become resistant to its derivative, methicillin (The new antibiotics, Holger Brethaupt, Nature Biotechnol 17,1999).

 Currently, the resistance of bacteria to the vast majority of known antibiotics poses a major public health problem. It has therefore become essential to develop new drugs to fight against bacterial infections according to mechanisms of action fundamentally different from current antibiotics.

 Moreover, it is known that the incidence of opportunistic fungal infections in humans has increased sharply in recent years.

 In particular, invasive fungal infections are very serious infections caused by fungi that are widespread in nature and whose pathogenic character appears in immunocompromised subjects, particularly following corticosteroids, chemotherapy, transplants, HIV infections, etc.

 Opportunistic fungal infections are currently a major cause of mortality in humans. They can be caused by yeasts, mainly of the genus Candida, or by filamentous fungi, in particular of the genus Aspergillus.

 In immunocompromised patients, it is common to observe the failure of antifungal treatments because of the toxicity of the latter (for example, amphotericin B), or the appearance of

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 resistant fungi (eg strains of Candida albicans are resistant to azole derivatives).

 Faced with such a situation, with serious health and social consequences, there is a real need to characterize new classes of antimicrobial compounds, especially antibacterial and antifungal compounds, in order to overcome the phenomenon of resistance that microorganisms have. developed or developed against the antimicrobial agents known to date.

 The present invention makes it possible to remedy this problem by proposing 3-deoxyanthocyanidin compounds having unexpected antimicrobial properties.

 Indeed, the antimicrobial activity of 3désoxyanthocyanidines compounds is described for the first time in the context of the present invention.

 Surprisingly, this antimicrobial activity is broad-spectrum, since these compounds are active not only against gram-positive and negative bacteria (antibacterial activity), but also against fungi and yeasts (antifungal activity).

 In this regard, the extent of their spectrum of activity make the 3-deoxyanthocyanidin compounds particularly interesting, and this, in many applications, in particular in the pharmaceutical, medical, cosmetic, phytosanitary and agri-food fields.

 According to a first aspect, the present invention relates to the use of at least one 3-deoxyanthocyanidine compound of formula (I):

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dans laquelle : (A) : a) : (1) Ri, R2, R3, R4, R5, R7, R8, R9, Rio et R11 désignent, indépendamment les uns des autres : - un atome d'hydrogène ; ou - un halogène ; ou - un groupe hydroxy ; un groupe alcoxy en Ci à C12 à chaîne droite ou ramifiée, saturée ou non ; un groupe acyloxy en Ci à
C12 à chaîne droite ou ramifiée, saturée ou non ; un groupe alkyle en
Ci à Ci2 à chaîne droite ou ramifiée, saturée ou non ; ou - un groupe nitro ; un groupe nitrile ; un radical comportant au moins un atome choisi parmi les atomes de silicium, de soufre et de phosphore ; ou - un groupe -O-glycosyl ; un groupe -O-glycosyl substitué par au moins un groupe alcoxy en Ci à C12 à chaîne droite ou ramifiée, saturée ou non ; un groupe acyloxy en Ci à C12 à chaîne droite ou ramifiée, saturée ou non ; un groupe alkyle en Ci à C12 à chaîne droite ou ramifiée, saturée ou non ; ou - un groupe alcényle en C2 à C30, linéaire ou ramifié, acyclique ou cyclique, ledit groupe étant éventuellement interrompu

in which: (A): a): (1) R 1, R 2, R 3, R 4, R 5, R 7, R 8, R 9, R 10 and R 11 denote, independently of one another: - a hydrogen atom; or - a halogen; or - a hydroxy group; a straight or branched chain C1-C12 alkoxy group, saturated or unsaturated; a C1 to C acyloxy group
C12 straight or branched chain, saturated or not; an alkyl group
Ci to C12 straight or branched chain, saturated or not; or - a nitro group; a nitrile group; a radical comprising at least one atom chosen from silicon, sulfur and phosphorus atoms; or - a -O-glycosyl group; a -O-glycosyl group substituted with at least one straight or branched chain C1-C12 alkoxy group, saturated or unsaturated; a straight or branched chain C1 to C12 acyloxy group, saturated or unsaturated; a straight or branched chain C1 to C12 alkyl group, saturated or unsaturated; or a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group being optionally interrupted

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 by at least one heteroatom, especially a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted by at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N-CY1Y2, in which Y1 and Y2 denote, independently of one another: # a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C 2 to C 30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - Y1 and Y2 together form a ring comprising from 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably chosen from carbon, nitrogen, oxygen and sulfur atoms, and said cycle being able to be substituted or not, aromatic or not; and (2) R6 denotes - a hydrogen atom; or - a halogen; or - a nitro group, a nitrile group, a radical comprising at least one atom chosen from silicon, sulfur and phosphorus atoms; or

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a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group optionally being interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted with minus a substituent other than a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N = CYiY2 in which Y1 and Y2 denote, independently of one another: # a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C 2 to C 30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 6 alkylaryl group
C30, said group being optionally substituted with at least one substituent different from a hydrogen atom; or b): (1) the substituents R 1 to R 11 are defined such that at least two substituents R 1 and R 1 + 1 (x = 1 to 10) together form a ring having from 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably selected from carbon, nitrogen, oxygen and sulfur, and said ring may be substituted or unsubstituted, aromatic or not; and

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(2) the substituents R 1 to R 10 other than the substituents R 1 and
Rx + 1 forming a ring, are as defined in (A); and (B): wherein X- represents: an anion derived from an organic acid, in particular an anion acetate, borate, citrate, tartrate, bisulfate, sulfate or phosphate; or an anion derived from a mineral acid, in particular anion bromide, chloride, borotetrafluoride or perchloride; or an anion derived from a sulfate or sulfonate group; for the preparation of a medicament for treating microbial infections in mammals, including humans.

 For this purpose, said 3-deoxyanthocyanidine compound is an antimicrobial agent, such as an antibacterial and / or antifungal agent.

 In particular, the medicament in question comprises at least one dexesoxyanthocyanidine as active ingredient, optionally combined with a pharmaceutically acceptable vehicle. Among these conventional vehicles, those skilled in the art may use diluents, adjuvants, excipients, etc.

 In addition, an antimicrobial drug according to the invention can be administered to a mammal, including the man, via any route, for example locally, orally, systemically, intravenously, intramuscularly, mucosally, using a patch. , or by incorporation or encapsulation in liposomes, microparticles, microcapsules, etc.

 The techniques for formulating and administering such medicaments are conventional in the field of the invention.

 The term halogen is used here according to the usual meaning, and represents indifferently chlorine, bromine, fluorine or iodine.

 For the purposes of the invention, the term "C1-C12 alkoxy group" means a group -OR, where R represents an aliphatic hydrocarbon chain containing from 1 to 12 carbon atoms, said chain

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 may be straight or branched, saturated or unsaturated. This definition includes methoxy, ethoxy, propoxy, n-butoxy, isobutoxy, sec-butoxy, t-butoxy, etc.

 The expressions straight chain and linear chain are equivalent and are used here indifferently in the conventional sense, well known to those skilled in the art.

 The term "branched chain" denotes chains containing at least one branch, with the exception of one ring. The chains comprising at least one cycle are identified as being cyclic.

 The term "C 1 -C 12 acyloxy group" denotes a group -COOR, where R represents an aliphatic hydrocarbon chain containing 1 to 12 carbon atoms, said chain may be straight or branched, saturated or unsaturated.

 In the context of the present invention, a C1-C12 alkyl group is a hydrocarbon group, saturated or unsaturated, straight or branched chain, having 1 to 12 carbon atoms. For example, such a group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, -CH 2 -t-butyl, cyclopropyl, pentyl, cyclopentyl, hexyl, cyclohexyl, cyclohexylmethyl, vinyl, allyl, etc. ...

 The term "radical" comprising at least one atom chosen from the atoms of silicon, sulfur and phosphorus, an alkoxy, acyloxy, alkyl or alkenyl group having at least one atom chosen from silicon, sulfur and phosphorus atoms. .

 By the term C 2 -C 30 alkenyl, here is meant a carbon chain comprising 2 to 30 carbon atoms and at least one olefinic double bond. The carbon chain can be linear or branched, cyclic or acyclic. Alkenyl is, for example, vinyl, allyl, etc.

 A heteroatom meets the conventional definition and represents an atom selected from oxygen, nitrogen and sulfur.

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 A C 6 -C 30 aryl group corresponds to a group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms by removal of a hydrogen atom. It may be substituted or unsubstituted, mononuclear or polymorphonuclear. Mention may be made, by way of illustration only, of mononuclear aryl radicals, phenyl, tolyl, etc. As polynuclear aryl radicals, naphthyl, anthryl, etc. are especially counted.

 By C 6 -C 30 aralkyl group, there is to be understood a C 6 -C 30 alkyl group containing an aryl group, said alkyl and aryl groups being as defined above.

 For the purposes of the invention, a C 6 to C 30 alkylaryl group is a C 6 to C 30 aryl group containing an alkyl group, said alkyl and aryl groups being as defined above.

 According to a second aspect, the present invention relates to the use of at least one 3-deoxyanthocyanidine compound of formula (I) as defined above, for the preparation of a cosmetic product.

 Such a cosmetic product advantageously has antimicrobial, i.e., antibacterial and / or antifungal properties.

 It can be presented in any suitable dosage form. By way of examples of cosmetic products suitable for the use of the 3-deoxyanthocyanidin compounds, mention may especially be made of make-up products, creams, lotions, balms, gels, aerosols, powders, dentifrices, solutions, soaps, etc. .., allowing application on the face and / or the body and / or in the mouth. For this purpose, the cosmetic products in question contain at least one 3-deoxyanthocyanidine associated, where appropriate, with one or more other useful compounds, as well as with a cosmetically acceptable carrier.

 According to a third aspect, the present invention relates to the use of at least one 3-deoxyanthocyanidine compound of formula (1), as described above, for combating microbial diseases in plants.

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 For this purpose, the plants are treated with at least one dexesoxyanthocyanidin according to conventional procedures in the phytosanitary field. In particular, it can be sprays on the leaves or at ground level, additions of the active compounds to the watering water by dissolving concentrated solutions, powders, tablets, tablets, so as to impregnate the soil , etc ...

 According to a fourth aspect, the present invention relates to the use of at least one 3-deoxyanthocyanidine compound of formula (1), for the preservation of products, preferably perishable foods.

 For example, in the agri-food sector, perishable foods, such as fresh products, dairy products, meat, fish, fruits and vegetables, should generally be protected, while preserving their quality. and this, especially during the preparation of ready meals, preserves, etc. The 3désoxyanthocyanidines compounds can advantageously be used for such purpose.

 According to a fifth aspect, the present invention relates to the use of at least one 3-deoxyanthocyanidine compound of formula (1) during the preparation of antimicrobial materials, such as fabrics, fabrics, polymers, papers, etc.

 In this context, at least one 3-deoxyanthocyanidin may be encapsulated in, or applied as dye to, said materials.

 According to a sixth aspect, the subject of the present invention is new 3-deoxyanthocyanidine compounds of formula (II):

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dans laquelle : (A) : les substituants : a) : (1) R1, R2, R4, R5, R7, R8, R9 et R11 désignent, indépendamment les uns des autres : - un atome d'hydrogène ; ou - un halogène ; ou - un groupe hydroxy ; un groupe alcoxy en Ci à C12 à chaîne droite ou ramifiée, saturée ou non ; un groupe acyloxy en Ci à C12 à chaîne droite ou ramifiée, saturée ou non ; un groupe alkyle en Ci à C12 à chaîne droite ou ramifiée, saturée ou non ; ou - un groupe nitro ; un groupe nitrile ; ou un radical comportant au moins un atome choisi parmi les atomes de silicium, de soufre et de phosphore ; ou - un groupe -O-glycosyl ; un groupe -O-glycosyl substitué par au moins un groupe alcoxy en Ci à C12 à chaîne droite ou ramifiée, saturée ou non ; un groupe acyloxy en Ci à C12 à chaîne droite ou ramifiée, saturée ou non ; un groupe alkyle en Ci à C12 à chaîne droite ou ramifiée, saturée ou non ; ou

wherein: (A): the substituents: a): (1) R1, R2, R4, R5, R7, R8, R9 and R11 denote, independently of one another: - a hydrogen atom; or - a halogen; or - a hydroxy group; a straight or branched chain C1-C12 alkoxy group, saturated or unsaturated; a straight or branched chain C1 to C12 acyloxy group, saturated or unsaturated; a straight or branched chain C1 to C12 alkyl group, saturated or unsaturated; or - a nitro group; a nitrile group; or a radical comprising at least one atom chosen from silicon, sulfur and phosphorus atoms; or - a -O-glycosyl group; a -O-glycosyl group substituted with at least one straight or branched chain C1-C12 alkoxy group, saturated or unsaturated; a straight or branched chain C1 to C12 acyloxy group, saturated or unsaturated; a straight or branched chain C1 to C12 alkyl group, saturated or unsaturated; or

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 a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group optionally being interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one a substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N = CYiY2, in which Y1 and Y2 denote, independently of one another: # a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted with minus a substituent other than a hydrogen atom; or an aryl group, an aralkyl group or a C6-C30 alkylaryl group, said group being optionally substituted with at least one substituent different from a hydrogen atom, or Y1 and Y2 together form a ring comprising From 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably selected from carbon, nitrogen, oxygen and sulfur, and said ring may be substituted or unsubstituted, aromatic or not; and (2) R3, R6, Rio denote, independently of one another: - a hydrogen atom; or - a halogen; or

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 a nitro group; a nitrile group; a radical comprising at least one atom chosen from an atom of silicon, sulfur and phosphorus; or a linear or branched, cyclic or acyclic C 2 to C 30 alkenyl group, said group optionally being interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted with at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N = CY1Y2, in which Y1 and Y2 denote, independently of one another: # a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted with minus a substituent other than a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or b): (1) the substituents R 1 to R 11 are defined such that at least two substituents R 1 and R 1 + 1 (x = 1 to 10) together form a ring having from 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably selected from

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carbon, nitrogen, oxygen and sulfur atoms, and said cycle may be substituted or unsubstituted, aromatic or not; and (2) Ri to Rio substituents other than Rx and
Rx + i forming a ring, are as defined in (A); and (B): wherein X- represents: - an anion derived from an organic acid, in particular an anion acetate, borate, citrate, tartrate, bisulfate, sulfate or phosphate; or an anion derived from a mineral acid, in particular anion bromide, chloride, borotetrafluoride or perchloride; or an anion derived from a sulphate or sulphonate group.

 In particular, such compounds are useful as drugs.

 According to a seventh aspect, the present invention relates to a process for preparing a 3-deoxyanthocyanidine compound as defined above.

According to a first embodiment, if, in the compound to be prepared, the substituent R7 is a hydrogen atom, said process comprises at least: the condensation in an acidic medium of an acetophenone (compound A) with an orthohydroxybenzaldehyde (compound B), according to the following reaction:

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According to a second embodiment, if, in the compound to be prepared, the substituent R7 is different from a hydrogen atom, said process comprises at least: the condensation in acid medium of a 1-phen-1 3-dione (compound A) with a phenol (compound B), according to the following reaction:

The following examples are intended to illustrate, without limitation, the present invention.

Exemple 1 : Synthèse du chlorure de 4',7,8-trihvdroxyflav,rlium
1 g de 4-hydroxyacétophénone (7,35 mmol) et 1,35 g de 2,3,4-trihydroxybenzaldéhyde (7,35 mmol) ont été dissous dans une solution de 40 ml d'acide formique contenant 10 % d'acide chlorhydrique EXAMPLES I. Materials and methods:
A- Examples of implementation of the processes for the preparation of
3-deoxyanthocyanidines according to the invention:
A-1 where R7 is a hydrogen atom:

Example 1 Synthesis of 4 ', 7,8-trihydroxyflavium chloride
1 g of 4-hydroxyacetophenone (7.35 mmol) and 1.35 g of 2,3,4-trihydroxybenzaldehyde (7.35 mmol) were dissolved in a solution of 40 ml of formic acid containing 10% of acid. hydrochloric

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 concentrated. The reaction mixture was stirred vigorously for 48 hours at room temperature and then evaporated to dryness in vacuo. The residue was washed several times with ether and then dissolved in 5 ml of 5% acidified methanol HCl. The 4 ', 7,8-trihydroxyflavylium chloride (red-burgundy) was recrystallized by slow addition of ether. The yield was 74%.

Analyzes carried out: UV: (nm) (0.1M HCl): 244.278 and 468.

1H Nuclear Magnetic Resonance (NMR): (200 MHz, DMSO-d 6 TFA-d, 298 K): 8.87 (1H, 8.8Hz, 8.33 (2H, 9.0Hz; H6 '), 8.05 (1H, 8.8 Hz, H3), 7.62 (1H, d, 9.0 Hz, 7.42 (1H, 8.9Hz, H6); 10 (2H, 9.0Hz, H3 ', H5').

Mass Spectrum: (FAB): m / e: (100M +) C15H11O4
Theoretical mass: Measured mass: 254.9Example 2: Synthesis of 7-N, N'-diethylamino-4'-aminoflavylium chloride
1 g of 4- (diethylamino) salicylaldehyde (5.17 mmol) and 0.704 g of 4'-aminoacetophenone (5.17 mmol) were dissolved in a solution of 50 ml of formic acid containing 10% concentrated hydrochloric acid. . The reaction mixture was stirred vigorously for 48 hours at room temperature and then evaporated to dryness in vacuo. The residue was washed several times with ether and then dissolved in 5 ml of methanol acidified with 10% HCl. The 7-N, N'-diethylamino-4'-aminoflavylium chloride (black) was recrystallized by slow addition of ether. The yield was 31%.

Analysis performed:

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Exemple 3 : Synthèse du chlorure de 3-undécanil-5-benzoflavylium
1,512 g de n-dodécanophénone et 1 g de 2-hydroxy-1- naphtaldéhyde ont été dissous dans 100 ml d'acétate d'éthyle auxquels ont été ajoutés 10 ml d'une solution d'acide bromohydrique dans de l'acide acétique à 48%. Le mélange réactionnel a été soumis à une agitation soutenue pendant 48 h à température ambiante. Une fois la réaction terminée, on a ajouté au milieu réactionnel 50 ml d'éther puis on a placé le mélange réactionnel au réfrigérateur pendant 12 h. Le mélange a été filtré puis le solide récupéré a été dissous dans le méthanol avec 2 ml d'acide chlorhydrique concentré. Le mélange a été mis au réfrigérateur puis filtré. La recristallisation a été effectuée une seconde fois. Le solide récupéré a été séché sous vide. On a obtenu 1431 mg d'une poudre rouge noire. Le rendement était de 57 %. 1H NMR: (300 MHz, CD30D, 298 K): 8.65 (1H, 8.8 Hz, H4); 8.23 (2H, dd, 6Hz, and H6 '); 7.87 (1H, 8.8Hz, 7.78 (1H, 9.0Hz, 7.37 (1H, 9.2Hz, H6), 7.23 (1H, H8); 96 (2H, d, 9.0 Hz, H3 ', H5'), 2.89 (4H, 1.30 (6H, 2 * CH3).

Example 3 Synthesis of 3-undecanilyl-5-benzoflavylium chloride
1.512 g of n-dodecanophenone and 1 g of 2-hydroxy-1-naphthaldehyde were dissolved in 100 ml of ethyl acetate to which was added 10 ml of a solution of hydrobromic acid in acetic acid to 48%. The reaction mixture was stirred for 48 h at room temperature. After the reaction was complete, 50 ml of ether was added to the reaction medium and the reaction mixture was then placed in the refrigerator for 12 hours. The mixture was filtered and the recovered solid was dissolved in methanol with 2 ml of concentrated hydrochloric acid. The mixture was refrigerated and filtered. Recrystallization was performed a second time. The recovered solid was dried under vacuum. 1431 mg of a black red powder were obtained. The yield was 57%.

Analysis carried out: 1 H NMR: (200 MHz, DMSO d6 / TFA d, K): 10.07 (1H, H4); 8. 95 (1H, d, 8.9Hz, 8.82 (1H, 9.1Hz, 8.45 (1H, 9.1Hz, 8.36 (2H, 9.0Hz; H2 ', H6'), 8.25 (1H, d, 9.1Hz, H8), 8.05 (1H, t, 8.0Hz, H6), 7.92 (1H, 8H, 0 Hz, 7.80 (1H, 7.8 Hz, 7.59 (2H, 9.0Hz, H3 ', H5').

Example 4 Synthesis of 4 ', 8-dimethylflavylium chloride
0.380 g of 2-hydroxy-3-methylbenzaldehyde and 0.372 g of 2-methylacetophenone were dissolved in 20 ml of ethyl acetate to which was added 5 ml of a solution of hydrobromic acid in acetic acid to 48%. The reaction mixture was subjected to

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 stirring continued for 48 h at room temperature. After the reaction was complete, 50 ml of ether were added to the reaction medium and the reaction mixture was then placed in the refrigerator for 12 hours. The recovered solid was dissolved in methanol with 2 ml of concentrated hydrochloric acid and then ether was added to the mixture. The mixture was refrigerated for 12 h and filtered. Recrystallization was performed a second time. The recovered solid was dried under vacuum. 322 mg of a red orange powder were obtained. The yield was 43%.

Exemple 5 : Synthèse du chlorure de 7,8-dihyhdroxL-4hénylflavylium
Dans cet exemple, R7 est un groupement phényle (C6H5-). Analysis carried out: 1 H NMR: (300 MHz, CD30D, 298 K): 9.45 (1H, 8.8 Hz, 8.80 (1H, d, 8.8 Hz, 8. 34 (1H, 9H) , 0 Hz, 8. 22 (1H, 9.0 Hz, 7. 80 (2H, d, 9.0Hz, H2 ', H6'), 7.62 (1H, 8.9Hz; , 02 (2H, 9.0 Hz, H3 ', H5'), 2. 89 (3H, CH3), 2.74 (3H, CH3) .A-2 where R7 is different from a hydrogen atom:

Example 5 Synthesis of 7,8-dihydroxy-4-enylflavylium chloride
In this example, R7 is a phenyl (C6H5-) group.

 1 g of pyrogallol (7.93 mmol) and 1.778 g of dibenzoylmethane (7.93 mmol) were dissolved in a solution of 50 ml of formic acid containing 10% concentrated hydrochloric acid. The reaction mixture was stirred vigorously for 48 hours at room temperature and then evaporated to dryness in vacuo. The residue was washed several times with ether and then dissolved in 5 ml of methanol acidified with 10% HCl. The 7,8-dihydroxy-4-phenyl flavylium chloride (brown-red) was recrystallized by slow addition of ether. The yield was 65%.

Analysis performed:

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 1H NMR: (300 MHz, CD30D, 298 K): 8.60 (2H, 6Hz, H2 'and H6'); 8.5 (1H, H3); 7.92-7.73 (9H, m; H3 ', H4', H5 ', H5, phenyl); 7.56 (1H, d, 9.2 Hz, H6).

 B-Examples of antifungal or antibacterial activity tests of 3-deoxyanthocyanidines according to the invention: Example 6: Tests of antifungal activities.

 The anti-Candida albicans and anti-Aspergillus fumigatus activities of the various 3-deoxyanthocyanidin molecules were evaluated by a liquid growth inhibition test carried out in 96-well microtiter plates or microplates.

 # Test against Candida albicans and anti-Candida glabrat.

The yeasts of the genus Candida were sown on slant agar plates of Sabouraud-Cloroamphenicol Agar (bioMérieux, Marcy l'Etoile, France) and incubated for 24 h at 30 ° C.

 Some yeast colonies were suspended in liquid Sabouraud medium (bioMérieux) in order to obtain a final concentration of 0.1 OD at 600 nm, corresponding to 2.5 × 10 6 cfu / ml.

The yeast suspension was adjusted to 5 × 10 3 cfu / ml in Sabouraud medium.

 10 μl of dilutions of 3-deoxyanthocyanidin samples were deposited in microtiter plates. Then, the inoculum containing the test microorganism was distributed in the wells to give a final volume of 100 l. The test plates were then placed in an incubator at 30 C for 16 to 18 hours.

 Control cultures were systematically performed by replacing 10 of sample with 10 l of sterile water. The sterility of

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 media was monitored by incubating 10 l of sterile water in the presence of 90 l of medium.

 Determination of minimal inhibitory concentrations (MIC) was performed by measuring the absorbance at 600 nm using a microtiter plate reader spectrophotometer. MIC was established for 50% growth inhibition.

 # Test anti - Aspergillus fumigatus.

Spores of Aspergillus fumigatus originated from a freezing stock at -80 C, titrated at 107 spores / ml in a 25% glycerol solution. After thawing slowly at room temperature, the spores were suspended in a PDB culture medium (12 g of Potato Dextrose Broth medium, Difco, (BioMerieux), for 1 ml of demineralized water).

10 l of each sample were plated in microtiter plate wells in the presence of 90 l of PDB culture medium, supplemented with tetracycline (100 g / ml) and cefotaxime (1 g / ml), and containing the spores (at a final concentration of 104 cfu / ml per well).

Control cultures were systematically performed in which 10 l of samples were replaced with 10 l of sterile water. The sterility of the media was monitored by incubating 10 l of sterile water in the presence of 90 μl of medium.

 The samples were incubated at 30 ° C. for 40 hours in a humid atmosphere and the antifungal activity was quantified by a score of 0 to 9 taking into account the germination. The size and morphology of the hyphae were determined under the binocular microscope. The IJC was a score of 4.

Example 7: Tests of antibacterial activities.

 The anti-Staphylococcus aureus and anti-Pseudomonas aeruginosa activities of the various 3-deoxyanthocyanidin molecules have been

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 evaluated by a growth inhibition test in a liquid medium made in 96-well titration microplates.

The samples were placed in the wells at a volume of 20 l, then an inoculum containing the microorganism in the appropriate medium was distributed in the wells, to give a final volume of 200 l.

# Test on Staphylococcus aureus (sensitive clinical strain IBS21)
The medium used was Luria-Bertani (LB). The inoculum was prepared from a freshly harvested bacterial culture after 6 hours of culture to obtain a density of 106 cfu / ml in the well.

 Control cultures were systematically performed, replacing 20 l of sample with 20 l of sterile water. The sterility of the media was monitored by incubating 20 liters of sterile water in the presence of 180 liters of medium.

 The microplates were then incubated for 16 to 18 hours at 37 ° C.

The determination of the MICs was carried out as indicated previously.

# Test on Staphylococcus aureus (clinical strain MRSA or
IBS04)
The medium used was LB medium. The inoculum was prepared from a freshly harvested bacterial culture after 6 hours of culture in order to obtain a density of 107 cfu / ml in the well.

Control cultures were systematically performed, replacing 20 l of sample with 20 l of sterile water. The sterility of the media was monitored by incubating 20 liters of sterile water in the presence of 180 μl of medium.

The microplates were then incubated for 16 to 18 hours at 37 ° C. The MICs were determined as described above.

 # Test on Pseudomonas aeruginosa:

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20 l of the different samples were deposited in the wells. An inoculum containing the microorganism in the appropriate medium was distributed in the wells to give a final volume of 200 μl.

 The medium used was LB medium. The inoculum was prepared from a freshly harvested bacterial culture after 6 hours of culture to obtain 0.001 units of optical density at 600 nm.

 Control cultures were systematically carried out under the same conditions as for the antibacterial activity tests above.

 The microplates were then incubated 16 to 18 hours at 30 C.

MICs were determined as described supra.

C-3-deoxyanthocyanidins studied in the context of the invention:
The following Table # specifies the identity and structure of the 3desoxyanthocyanidin compounds tested according to the procedures given in Part B supra (Examples 6 and 7).

II. Experimental results :
The following Table II provides the MIC values obtained for 3-deoxyanthocyanidin compounds that have been tested for their antifungal and / or antibacterial properties as described in Part B above.

 MICs are expressed in μg / mL.

<Desc / Clms Page number 24>

<Tb>

S <SEP> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> R5 <SEP> R6 <SEP> R7 <SEP> R8 <SEP> R9 <SEP> R10 <SEP> R11 <SEP> xNAME <MS> N <SEP> 3 '<SEP>4'<SEP> 5 '<SEP>6'<SEP> 3 <SEP> 4 <SEP> 5 <SEP> 7
<tb> Chloride <SEP> of <SEP> 3 ', 4'-dihydroxy-3,7-dimethoxy <SEP> flavylium <SEP> 3 <SEP> OH <SEP> OCH3 <SEP> OCH3
<tb> Chloride <SEP> of <SEP> 4 ', 7,8-trihydroxy <SEP> flavylium <SEP> 4 <SEP> OH <SEP> OH <SEP> OH <SEP> Cl
<Tb>

Chlorure 2-a-naphthyl-l-(7,8-dihydroxy)- Benzo OH OH ciChlorure de 2-a-naphthyl-1-(7,8-dihydroxy)- . Benzo Chlorure de 2-p-naphthyl-l-(7,8-dihydroxy)- 6 Benzo OH ci-

2-α-naphthyl-1- (7,8-dihydroxy) -benzylchloride chloride 2-a-naphthyl-1- (7,8-dihydroxy) chloride. Benzo 2-p-naphthyl-1- (7,8-dihydroxy) -6-benzohexyl chloride

<tb><SEP> Chloride <SEP> 7,8-dihydroxy-3 ', 4', 5'-trimethoxy <SEP> flavylium <SEP> 7 <SEP> OCH3 <SEP> OCH3 <SEP> OCH3 <SEP> OH <SEP> OH <SEP> CI '
<tb> Chloride <SEP> of <SEP> 4 ', 7,8-trihydroxy-3'methoxy <SEP> flavylium <SEP> 8 <SEP> OCH3 <SEP> OH <SEP> OH <SEP> OH <SEP> Chloride <SEP> of <SEP> 3 ', <SEP>4', 7,8-tetrahydroxy <SEP> flavylium <SEP> 9 <SEP> OH <SEP> OH <SEP> OH <SEP> OH <SEP> ClBromide <SEP> of <SEP> 3 ', <SEP>4', 7,8-tetrahydroxy <SEP> flavylium <SEP> 10 <SEP> OH <SEP> OH <SEP> OH <SEP> OH <SEP> Br
<tb> Chloride <SEP> of <SEP>7,8-dihydroxy-4'-methyl<SEP> flavylium <SEP> 13 <SEP> CH3 <SEP> OH <SEP> OH <SEP> Chloride <SEP> from <SEP> 7,8-dihydroxy-3 ', 4-dimethyl <SEP> flavylium <SEP> 16 <SEP> CH3 <SEP> CH3 <SEP> OH <SEP> OH <SEP> ClCloride <SEP> from <SEP> 7 8-dihydroxy-2 ', 4'-dimethyl-SEP-flavylium-SEP-17-SEP-CH3-SEP-CH3-SEP-pTIi-SEP-OH-SEP-OH-SEP-Chloride-SEP-SEP > 7,8-dihydroxy-2 ', <SEP>4',5'-trimethyl<SEP> flavylium <SEP> 18 <SEP> CH3 <SEP> CH3 <SEP> CH3 <SEP> OH <SEP> OH <SEP > Chloride <SEP> of <SEP>7,8-dihydroxy-4'-methoxy<SEP> flavylium <SEP> 23 <SEP> OCH3 <SEP> OH <SEP> OH <SEP> Cl-
<Tb>

<Desc / Clms Page number 25>

<tb> Table <SEP>#<SEP> (continued)
<tb> S <SEP> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> R5 <SEP> R6 <SEP> R7 <SEP> R8 <SEP> R9 <SEP> R10 <SEP> R11 <SEP > XNOM <SEP> N <SEP> 2 '<SEP>3'<SEP> 4 '<SEP>5'<SEP> 6 '<SEP> 3 <SEP> 4 <SEP> 5 <SEP> 6 <SEP><SEP> 8 <SEP> X-Chloride <SEP> of <SEP> 4-trifluoromethyl-7,8-dihydroxy <SEP> flavylium <SEP> 25 <SEP> CF3 <SEP> OH <SEP> OH <SEP> ClCloride <SEP><SEP> 7,8-dihydroxy-4-phenyl <SEP> flavylium <SEP> 26 <SEP> Phenyl <SEP> OH <SEP> OH <SEP> Chloride <SEP> of <SEP> 7.8, 2 ', 3', 4'-pentahydroxy <SEP> flavylium <SEP> 29 <SEP> OH <SEP> OH <SEP> OH <SEP> OH <SEP> OH <SEP> ClCloride <SEP> from <SEP> 2 ', 7,8-trihydroxy'SEP> flavylium <SEP> 30 <SEP> OH <SEP> OH <SEP> OH <SEP> CI '
<tb> Chloride <SEP> of <SEP> 7,8-dihydroxy <SEP> flavylium <SEP> 31 <SEP> OH <SEP> OH <SEP> ClChloride <SEP> of <SEP> 7-N, N'- diethylamino-3 ', 4'-dihydroxy <SEP> flavylium <SEP> 32 <SEP> OH <SEP> OH <SEP> N (Et) 2 <SEP> ClChloride <SEP> of <SEP>4'-hydroxy<SEP> flavylium <SEP> 34 <SEP> OH <SEP> ClChloride <SEP> of <SEP>4'-hydroxy-3'-methoxy<SEP> flavylium <SEP> 38 <SEP> OCH3 <SEP> OH <SEP> ClChloride <SEP> of <SEP> 3 ', 4'-dihydroxy <SEP> flavylium <SEP> 39 <SEP> OH <SEP> OH <SEP> ClChloride <SEP> of <SEP>2',5'-dimethyl<SEP> flavylium <SEP> 42 <SEP> CH3 <SEP> CH3 <SEP> ClChloride <SEP> of <SEP>3'-hydroxy<SEP> flavylium <SEP> 44 <SEP> OH <SEP> Chloride <SEP> from <SEP>2'-methoxy<SEP> flavylium <SEP> 45 <SEP> OCH3 <SEP> ClChloride <SEP> from <SEP> 3 ', 5'-dihydroxy <SEP> flavylium <SEP> 46 <SEP> OH <SEP > OH <SEP> Chloride <SEP> of <SEP> 4 ', 7-dihydroxy <SEP> flavylium <SEP> 51 <SEP> OH <SEP> OH <SEP> ClCloride <SEP> from <SEP> 2-a- naphthyl-1- (7-hydroxy) -benzopyrilium <SEP> 52 <SEP> Be <Sep>SEP> CHCl 3 <SEP><SEP>7-hydroxy-2'-methyl<SEP> flavylium <SEP> 57 <SEP> CH3 <SEP> OH <SEP> Chloride <SEP> from <SEP > 7-hydroxy-3-undecanyl <SEP> flavylium <SEP> 58 <SEP> (CH2) 10-CH3 <SEP> OH <SEP> ClChloride <SEP> of <SEP>7-hydroxy-4'-methyl<SEP> flavylium <SEP> 60 <SEP> CH3 <SEP> OH <SEP> Chloride <SEP> of <SEP> 7-hydroxy-2 ', 4'-dimethyl <SEP> flavylium <SEP> 63 <SEP> CH3 <SEP > CH3 <SEP> OH <SEP> CHCl 3 <SEP> 7-hydroxy-2 ', 4', 5'-trimethyl <SEP> flavylium <SEP> 64 <SEP> CH3 <SEP> CH3 <SEP> CH3 <SEP> OH <SEP> Cl-
<Tb>

<Desc / Clms Page number 26>

<tb> Table <SEP> 1 <SEP> (continued) <SEP>
<tb> S <SEP> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> R5 <SEP> R6 <SEP> R7 <SEP> R8 <SEP> R9 <SEP> R10 <SEP> R11 <SEP > XNOM <SEP> N <SEP> 2 '<SEP>3'<SEP> 4 '<SEP> - <SEP>5'<SEP> 6 '<SEP> 3 <SEP> 4 <SEP> 5 <SEP><SEP> 7 <SEP> 8 <SEP> XChloride <SEP> of <SEP> 3 ', 5', 7-trihydroxy <SEP> flavylium <SEP> 68 <SEP> OH <SEP> OH <SEP> OH <SEP> CI '
<tb> Chloride <SEP> of <SEP> 4 ', 7-dihydroxy-3-methyl <SEP> flavylium <SEP> 69 <SEP> OH <SEP> CH3 <SEP> OH <SEP> Cl
<Tb>

Chlorure de 7-hydroxy-4'-O-C=O(CH2)wCH3 flavylium 75 OH ci-

Chloride of 7-hydroxy-4'-OC = O (CH2) wCH3 flavylium 75 OH ci-

<tb> Chloride <SEP> of <SEP> 2 ', <SEP>4',7-Trihydroxy-3'-methyl<SEP> flavylium <SEP> 76 <SEP> OH <SEP> CH3 <SEP> OH <SEP > OH <SEP> ClCloride <SEP> of <SEP> 2 ', <SEP>3',<SEP> 4 ', <SEP> 7-tetrahydroxy <SEP> flavylium <SEP> 77 <SEP> OH <SEP> OH <SEP> OH <SEP> OH <SEP> CI '
<tb> Chloride <SEP> of <SEP> 2 ', 7-dihydroxy <SEP> flavylium <SEP> 78 <SEP> OH <SEP> OH <SEP> ClChloride <SEP> from <SEP>3',<SEP> 4 ', <SEP> 5, <SEP> 7-tetrahydroxy <SEP> flavylium <SEP> 80 <SEP> OH <SEP> OH <SEP> OH <SEP> OH <SEP> ClCloride <SEP> from <SEP> 5 7-dihydroxy-4'-methoxy <SEP> flavylium <SEP> 82 <SEP> OCH3 <SEP> OH <SEP> OH <SEP> ClChloride <SEP> of <SEP> 5,7,2 ', 4', 6'-pentahydroxy-3-methoxy <SEP> 85 <SEP> OH <SEP> OH <SEP> OH <SEP> OCH3 <SEP> OH <SEP> OH <SEP> ClCloride <SEP> from <SEP> 4 ', 5,7-trihydroxy-3-methoxy <SEP> flavylium <SEP> 86 <SEP> OH <SEP> OCH3 <SEP> OH <SEP> OH <SEP> ClCloride <SEP> from <SEP> 3 ', 4', 6-trihydroxy <SEP> flavylium <SEP> 93 <SEP> OH <SEP> OH <SEP> OH <SEP> ClCloride <SEP> of <SEP>6-hydroxy-4'-amino<SEP> flavylium <SEP> 94 <SEP> NH2 <SEP> OH <SEP> Chloride <SEP> of <SEP>6-hydroxy-2'-methoxy<SEP> flavylium <SEP> 96 <SEP> OCH3 <SEP> OH <SEP> Chloride <SEP> of <SEP>4'-hydroxy-6-nitro<SEP> flavylium <SEP> 98 <SEP> OH <SEP> NO2 <SEP> CI
<tb> Chloride <SEP> of <SEP> 3 ', 4', 8-trihydroxy <SEP> flavylium <SEP> 104 <SEP> OH <SEP> OH <SEP> OH <SEP> CI '
<tb> Chloride <SEP> of <SEP> 3 ', 4', 6,7-tetrahydroxy <SEP> flavylium <SEP> 106 <SEP> OH <SEP> OH <SEP> OH <SEP> OH <SEP> CI '
<tb> Chloride <SEP> of <SEP>5,6-benzyl-4'-hydroxy<SEP> flavylium <SEP> 107 <SEP> OH <SEP> Benzo <SEP> CI '
<tb> Chloride <SEP> of <SEP> 2-a-naphthyl-1-naphthopyrilium <SEP> 108 <SEP> Benzo <SEP> Benzo <SEP> CI '
<tb> Chloride <SEP> of <SEP> 5,6-benzyl-3 ', 4', 5'-trimethoxy <SEP> flavylium <SEP> 110 <SEP> OCH3 <SEP> OCH3 <SEP> OCH3 <SEP> Benzo <SEP> CI '
<tb> Chloride <SEP> of <SEP> 5,6-benzyl-3 ', 4'-dihydroxy <SEP> flavylium <SEP> 111 <SEP> OH <SEP> OH <SEP> Benzo <SEP>CI'
<Tb>

<Desc / Clms Page number 27>

<tb> Table <SEP>#<SEP> (continued)
<tb> S <SEP> R1 <SEP> R2 <SEP> R3 <SEP> R4 <SEP> R5 <SEP> R6 <SEP> R7 <SEP> R8 <SEP> R9 <SEP> R10 <SEP> R11 <SEP > XNOM <SEP> N <SEP> 2 '<SEP>3'<SEP> 4 '<SEP> 5- <SEP>6'<SEP> 3 <SEP> 4 <SEP> 5 <SEP> 6 <SEP> 7 <SEP> 8 <SEP> X- <SEP>
<tb> Chloride <SEP> of <SEP>5,6-benzyl-2'-methyl<SEP> flavylium <SEP> 112 <SEP> CH3 <SEP> Benzo <SEP> CI '
<tb> Chloride <SEP> of <SEP> 5,6-benzyl-2 ', 5'-dihydroxy <SEP> flavylium <SEP> 116 <SEP> OH <SEP> OH <SEP> Benzo <SEP> CIChloride <SEP <SEP> 5,6-benzyl-3 ', 4'-dimethyl <SEP> flavylium <SEP> 118 <SEP> CH3 <SEP> CH3 <SEP> Benzo <SEP> ClChloride <SEP> from <SEP> 5 , 6-benzyl-2 ', 4'-dimethyl-SEP-flavylium-SEP-119-SEP-CH3-SEP-CH3-SEP-Benzo-SEP-CH4-Chloride-SEP-5,6-benzyl-3 'SEQ ID NOV'><SEP> 5-benzyl-3 ', 5'-dihydroxy <SEP> 5-dihydroxy-phenylphosphonate <SEP><SEP> OH <SEP> OH <SEP> Benzo <SEP> CCHhloride <SEP> of <SEP>5,6-benzyl-4'-hydroxy-3-methyl<SEP> flavylium <SEP> 123 <SEP> CH3 <SEP> OH <SEP> Benzo <SEP> CIChloride <SEP> of <SEP> 2 ', 4'-dihydroxy-5,7-dimethoxy <SEP> flavylium <SEP> 127 <SEP> OH <SEP> OH <SEP > OCH3 <SEP> OCH3 <SEP> CI '
<tb> Chloride <SEP> of <SEP> 2 ', 4'-dihydroxy-5,7-dimethoxy-3'-methyl <SEP> 129 <SEP> OH <SEP> OH <SEP> CH3 <SEP> OCH3 <SEP> OCH3 <SEP> Clflavylium <SEP> ~~~~~ <SEP> ~~~~~ <SEP> ~~~ <SEP> ~~~~ <SEP> ~~~~
<tb> Chloride <SEP> of <SEP>6,8-dibromo-4'-hydroxy<SEP> flavylium <SEP> 130 <SEP> OH <SEP> Br <SEP> Br <SEP> ClChloride <SEP> from <MS> 6,8-dibromo-3 ', 5'-hydroxy <SEP> flavylium <SEP> 133 <SEP> OH <SEP> OH <SEP> Br <SEP> Br <SEP> Cl-
<Tb>

<Desc / Clms Page number 28>

<tb> Tableau <SEP> It
<tb> NAME <SEP> Staphylococcus <SEP> Staphylococcus <SEP> Pseudomonas <SEP> Candida <SEP> Candida <SEP> Aspergillus
<tb> aureus <SEP> aureus <SEP> Pseudomonas <SEP> albicans <SEP> glabrata <SEP> fumigatus
<tb> strain <SEP> 21 <SEP> MRSA <SEP> aerugmosa <SEP> IHEM <SEP> 8060 <SEP> patient <SEP> 1 <SEP> GASP <SEP> 4707 <SEP>
<tb> Chloride <SEP> of <SEP> 3 ', <SEP>4'-dihydroxy-3,7-dimethoxy<SEP> flavylium <SEP> 3 <SEP><30<SEP><30<SEP>> 60 <SEP><60<SEP><60<SEP>> 60
<tb> Chloride <SEP> of <SEP> 4 ', 7,8-trihydroxy <SEP> flavylium <SEP> 4 <SEP><<SEP> 3.0 <SEP><60<SEP><30<SEP>> 60 <SEP><60<SEP>> 60
<tb><SEP> 2-α-naphthyl-1- (7,8-dihydroxy) -benzopyrilium <SEP> Chloride <SEP><SEP><<SEP> 0.3 <SEP><60<SEP><60<SEP><60<SEP><60<SEP>> 60
<Tb>

Chlorure de 2-p-naphthyl-1-(7,8-dihydroxy)-benzopyrilium 6 < 3,0 <60 >60 <60 <30 >60

2-p-naphthyl-1- (7,8-dihydroxy) -benzopyrilium chloride 6 <3.0 <60> 60 <60 <30> 60

<tb><SEP> Chloride <SEP> 7,8-dihydroxy-3 ', 4', 5'-trimethoxy <SEP> flavylium <SEP> 7 <SEP><30<SEP><30<SEP>> 60 <SEP><30<SEP><30<SEP>> 60
<tb> Chloride <SEP> of <SEP> 4 ', 7,8-trihydroxy-3'-methoxy <SEP> flavylium <SEP><<SEP> 3.0 <SEP><60<SEP><60<SEP><30<SEP><30<SEP>> 60
<tb> Chloride <SEP> of <SEP> 3 ', 4', 7,8-tetrahydroxy <SEP> flavylium <SEP> 9 <SEP><<SEP> 3.0 <SEP><30<SEP><30<SEP><30<SEP><30<SEP>> 60
<tb> Bromide <SEP> of <SEP> 3 ', 4', 7,8-tetrahydroxy <SEP> flavylium <SEP> 10 <SEP><<SEP> 3.0 <SEP><60<SEP><30<SEP><30<SEP><30<SEP>> 60
<tb> Chloride <SEP> of <SEP>7,8-dihydroxy-4'-methyl<SEP> flavylium <SEP> 13 <SEP><<SEP> 0.3 <SEP><30<SEP><60<SEP><30<SEP><30<SEP>> 60
<tb> Chloride <SEP> of <SEP> 7,8-dihydroxy-3 ', 4'-dimethyl <SEP> flavylium <SEP> 16 <SEP><<SEP> 0.3 <SEP><60<SEP><60<SEP><60<SEP><30<SEP><60
<tb> Chloride <SEP> of <SEP> 7,8-dihydroxy-2 ', <SEP>4'-dimethyl<SEP> flavylium <SEP> 17 <SEP><<SEP> 3.0 <SEP><60<SEP><30<SEP><30<SEP><30<SEP><60
<tb> Chloride <SEP> of <SEP> 7,8-dihydroxy-2 ', 4', 5'-trimethyl <SEP> flavylium <SEP> 18 <SEP><<SEP> 3.0 <SEP><30<SEP><60<SEP><30<SEP><30<SEP><60
<tb> Chloride <SEP> of <SEP>7,8-dihydroxy-4'-methoxy<SEP> flavylium <SEP> 23 <SEP><<SEP> 3.0 <SEP><60<SEP><60<SEP><60<SEP><30<SEP>> 60
<tb> Chloride <SEP> of <SEP> 4-trifluoromethyl-7,8-dihydroxy <SEP> flavylium <SEP> 25 <SEP><<SEP> 3.0 <SEP><60<SEP><SEP> 3.0 <SEP><<SEP> 3.0 <SEP><<SEP> 3.0 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 7,8-dihydroxy-4-phenyl <SEP> flavylium <SEP> 26 <SEP><<SEP> 3.0 <SEP><60<SEP><30<SEP><30<SEP><60<SEP>> 60
<tb> Chloride <SEP> of <SEP> 7,8,2 ', 3', 4'-pentahydroxy <SEP> flavylium <SEP> 29 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP><30<SEP><30<SEP>> 60
<tb> Chloride <SEP> of <SEP> 2 ', 7,8-trihydroxy <SEP> flavylium <SEP> 30 <SEP><<SEP> 3.0 <SEP><30<SEP><30<SEP><30<SEP><30<SEP>> 60
<tb> Chloride <SEP> of <SEP> 7,8-dihydroxy <SEP> flavylium <SEP> 31 <SEP><<SEP> 3.0 <SEP><60<SEP><60<SEP><30<SEP><30<SEP>> 60
<tb><SEP> Chloride <SEP> 7-N, N'-diethylamino-3 ', 4'-dihydroxy <SEP> flavylium <SEP> 32 <SEP><<SEP> 3.0 <SEP><60<SEP><60<SEP><30<SEP><30<SEP>> 60
<tb> Chloride <SEP> of <SEP>4'-hydroxy<SEP> flavylium <SEP> 34 <SEP><<SEP> 3.0 <SEP><<SEP> 3.0 <SEP><60<SEP><60<SEP><60<SEP><60
<Tb>

<Desc / Clms Page number 29>

<tb> Table <SEP> It <SEP> (continued)
<tb> NAME <SEP> Staphylococcus <SEP> Staphylococcus <SEP> Pseudomonas <SEP> Candida <SEP> Candida <SEP> Aspergillus
<tb> aureus <SEP> aureus <SEP> Pseudomonas <SEP> albicans <SEP> glabrata <SEP> fumigatus
<tb> strain <SEP> 21 <SEP> MRSA <SEP> aerugmosa <SEP> IHEM <SEP> 8060 <SEP> patient <SEP> 1 <SEP> GASP <SEP> 4707 <SEP>
<tb> Chloride <SEP> of <SEP>4'-hydroxy-3'-methoxy<SEP> flavylium <SEP> 38 <SEP><<SEP> 3.0 <SEP><30<SEP>> 60 <SEP ><60<SEP><60<SEP>> 60
<tb> Chloride <SEP> of <SEP> 3 ', 4'-dihydroxy <SEP> flavylium <SEP> 39 <SEP><<SEP> 0.3 <SEP><60<SEP><60<SEP><<SEP><30<SEP><60
<tb> Chloride <SEP> of <SEP> 2 ', <SEP>5'-dimethyl<SEP> flavylium <SEP> 42 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP>> 60 <SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP>3'-hydroxy<SEP> flavylium <SEP> 44 <SEP><<SEP> 0.3 <SEP><<SEP> 3.0 <SEP>> 60 <SEP >> 60 <SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP>2'-methoxy<SEP> flavylium <SEP> 45 <SEP><30<SEP><60<SEP>> 60 <SEP><<SEP> 3.0 <SEP >> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 3 ', <SEP>5'-dihydroxy<SEP> flavylium <SEP> 46 <SEP><<SEP> 0.3 <SEP><30<SEP><60<SEP>> 60 <SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 4 ', <SEP> 7-dihydroxy <SEP> flavylium <SEP> 51 <SEP><<SEP> 0.3 <SEP><60<SEP><60<SEP><60<SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 2 ', 3'-benzyl-7-hydroxy <SEP> flavylium <SEP> 52 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP><30<SEP><30<SEP><60
<tb> Chloride <SEP> of <SEP>7-hydroxy-2'-methyl<SEP> flavylium <SEP> 57 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP><30<SEP><30<SEP><60
<tb> Chloride <SEP> of <SEP> 7-hydroxy-3-undecanyl <SEP> flavylium <SEP> 58 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP>> 60 <SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP>7-hydroxy-4'-methyl<SEP> flavylium <SEP> 60 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP><30<SEP><60<SEP>> 60
<tb><SEP> Chloride <SEP> 7-hydroxy-2 ', 4'-dimethyl <SEP> flavylium <SEP> 63 <SEP><<SEP> 3.0 <SEP><30<SEP>> 60 <SEP><30<SEP><30<SEP><30
<tb> Chloride <SEP> of <SEP> 7-hydroxy-2 ', <SEP>4',5'-trimethyl<SEP> flavylium <SEP> 64 <SEP><<SEP> 0.3 <SEP><<SEP>> 60 <SEP><30<SEP><30<SEP><30
<tb> Chloride <SEP> of <SEP> 3 ', <SEP>5', 7-trihydroxy <SEP> flavylium <SEP> 68 <SEP><<SEP> 3.0 <SEP><60<SEP><<SEP><30<SEP><30<SEP>> 60
<tb> Chloride <SEP> of <SEP> 4 ', 7-dihydroxy-3-methyl <SEP> flavylium <SEP> 69 <SEP><<SEP> 3.0 <SEP><30<SEP>> 60 <SEP>> 60 <SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP>7-hydroxy-4'-OC = O (CH2) 14-CH3 <SEP> flavylium <SEP> 75 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP><60<SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 2 ', <SEP>4',<SEP>7-Trihydroxy-3'-methyl<SEP> flavylium <SEP> 76 <SEP><<SEP> 0.3 <SEP><60<SEP>> 60 <SEP>> 60 <SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 2 ', <SEP>3',<SEP> 4 ', <SEP> 7-tetrahydroxy <SEP> flavylium <SEP> 77 <SEP><<SEP> 3.0 <SEP><30<SEP><30<SEP><30<SEP><30<SEP>> 60
<tb> Chloride <SEP> of <SEP> 2 ', 7-dihydroxy <SEP> flavylium <SEP> 78 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP><60<SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 3 ', <SEP>4',<SEP> 5, <SEP> 7-tetrahydroxy <SEP> flavylium <SEP> 80 <SEP><<SEP> 0.3 <SEP><60<SEP><30<SEP><60<SEP><30<SEP>> 60
<Tb>

<Desc / Clms Page number 30>

<tb> Table <SEP> It <SEP> (continued)
<tb> NAME <SEP> Staphylococcus <SEP> Staphylococcus <SEP> Pseudomonas <SEP> Candida <SEP> Candida <SEP> Aspergillus
<tb> aureus <SEP> aureus <SEP> Pseudomonas <SEP> albicans <SEP> glabrata <SEP> fumigatus
<tb> strain <SEP> 21 <SEP> MRSA <SEP> aeruginosa <SEP> IHEM <SEP> 8060 <SEP> patient <SEP> 1 <SEP> GASP <SEP> 4707 <SEP>
<tb> Chloride <SEP> of <SEP>5,7-dihydroxy-4'-methoxy<SEP> flavylium <SEP> 82 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP>> 60 <SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 5,7,2 ', 4', 6'-pentahydroxy-3-methoxy <SEP> flavylium <SEP> 85 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP><30<SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 4 ', 5,7-trihydroxy-3-methoxy <SEP> flavylium <SEP> 86 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP>> 60 <SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 3 ', 4', 6-trihydroxy <SEP> flavylium <SEP> 93 <SEP><<SEP> 3.0 <SEP><60<SEP><30<SEP><30<SEP><30<SEP>> 60
<tb> Chloride <SEP> of <SEP>6-hydroxy-4'-amino<SEP> flavylium <SEP> 94 <SEP><<SEP> 3.0 <SEP><<SEP> 3.0 <SEP><30<SEP><30<SEP><30<SEP>> 60
<tb> Chloride <SEP> of <SEP>6-hydroxy-2'-methoxy<SEP> flavylium <SEP> 96 <SEP><<SEP> 0.3 <SEP><60<SEP>> 60 <SEP>> 60 <SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP>4'-hydroxy-6-nitro<SEP> flavylium <SEP> 98 <SEP><<SEP> 3.0 <SEP><30<SEP><60<SEP>> 60 <SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 3 ', <SEP>4', 8-trihydroxy <SEP> flavylium <SEP> 104 <SEP><<SEP> 3.0 <SEP><30<SEP><<SEP><30<SEP><30<SEP>> 60
<tb> Chloride <SEP> of <SEP> 3 ', 4', 6,7-tetrahydroxy <SEP> flavylium <SEP> 106 <SEP><<SEP> 3.0 <SEP><60<SEP><<SEP> 3.0 <SEP><30<SEP><30<SEP>> 60
<tb> Chloride <SEP> of <SEP>5,6-benzyl-4'-hydroxy<SEP> flavylium <SEP> 107 <SEP><<SEP> 3.0 <SEP><30<SEP>> 60 <SEP><SEP> 0.3 <SEP><SEP> 3.0 <SEP><SEP> 3.0 SEP>
<tb> Chloride <SEP> of <SEP> (5.6), <SEP> (2 ', <SEP>3') - dibenzyl <SEP> flavylium <SEP> 108 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP>> 60 <SEP>> 60 <SEP>> 60
<tb><SEP> Chloride <SEP> 5,6-benzyl-3 ', 4', 5'-trimethoxy <SEP> flavylium <SEP> 110 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP><30<SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 5,6-benzyl-3 ', 4'-dihydroxy <SEP> flavylium <SEP> 111 <SEP><30<SEP><60<SEP><30<SEP><<SEP> 0.3 <SEP><<SEP> 3.0 <SEP><SEP> 3.0
<tb> Chloride <SEP> of <SEP>5,6-benzyl-2'-methyl<SEP> flavylium <SEP> 112 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP>> 60 <SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 5,6-benzyl-2 ', <SEP>5'-dihydroxy<SEP> flavylium <SEP> 116 <SEP><<SEP> 3.0 <SEP><30<SEP>> 60 <SEP><30<SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 5,6-benzyl-3 ', <SEP>4'-dimethyl<SEP> flavylium <SEP> 118 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP>> 60 <SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 5,6-benzyl-2 ', <SEP>4'-dimethyl<SEP> flavylium <SEP> 119 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP><30<SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP>5,6-benzyl-3'-hydroxy<SEP> flavylium <SEP> 121 <SEP><<SEP> 3.0 <SEP><30<SEP>> 60 <SEP><30<SEP><30<SEP><60
<tb> Chloride <SEP> of <SEP> 5,6-benzyl-3 ', <SEP>5'-dihydroxy<SEP> flavylium <SEP> 122 <SEP><<SEP> 3.0 <SEP><<SEP> 3.0 <SEP><60<SEP><30<SEP><60<SEP>> 60
<tb> Chloride <SEP> of <SEP>5,6-benzyl-4'-hydroxy-3-methyl<SEP> flavylium <SEP> 123 <SEP><<SEP> 3.0 <SEP><30<SEP>> 60 <SEP><30<SEP><30<SEP><30
<Tb>

<Desc / Clms Page number 31>

<tb> Tableau <SEP> It <SEP> (continued) <SEP>
<tb> NAME <SEP> Staphylococcus <SEP>'SEP> Staphylococcus <SEP> Pseudomonas <SEP> Candida <SEP> Candida <SEP> Aspergillus
<tb> aureus <SEP> @ <SEP> aureus <SEP> Pseudomonas <SEP> albicans <SEP> glabrata <SEP> fumigatus
<tb> strain <SEP> 21 <SEP> MRSA <SEP> aerugmosa <SEP> IHEM <SEP> 8060 <SEP> patient <SEP> 1 <SEP> GASP <SEP> 4707 <SEP>
<tb> Chloride <SEP> of <SEP> 2 ', 4'-dihydroxy-5,7-dimethoxy <SEP> flavylium <SEP> 127 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP>> 60 <SEP>> 60 <SEP>> 60
<tb> Chloride <SEP> of <SEP> 2 ', <SEP>4'-dihydroxy-5,7-dimethoxy-3'-methyl<SEP> flavylium <SEP> 129 <SEP><<SEP> 0.3 <SEP><60<SEP>> 60 <SEP><60<SEP><60<SEP>> 60
<tb> Chloride <SEP> of <SEP>6,8-dibromo-4'-hydroxy<SEP> flavylium <SEP> 130 <SEP><<SEP> 3.0 <SEP><<SEP> 3.0 <SEP><60<SEP><30<SEP><60<SEP><60
<tb> Chloride <SEP> of <SEP> 6,8-dibromo-3 ', 5'-hydroxy <SEP> flavylium <SEP> 133 <SEP><<SEP> 3.0 <SEP><60<SEP>> 60 <SEP><30<SEP>> 60 <SEP>> 60
<Tb>

Claims (12)

C1 to C12 straight or branched chain, saturated or not; or - a nitro group; a nitrile group; a radical comprising at least one atom chosen from silicon, sulfur and phosphorus atoms; or - a -O-glycosyl group; a -O-glycosyl group substituted with at least one straight chain C1-C12 alkoxy group or C12 straight or branched chain, saturated or not; an alkyl group  wherein: (A): a): (1) R 1, R 2, R 3, R 4, R 5, R 7, R 8, R 9, R 10 and R 11 denote, independently of one another: - a hydrogen atom; or - a halogen; or - a hydroxyl group, a straight or branched chain C1-C12 alkoxy group, saturated or unsaturated; a C1 to C acyloxy group

 1. Use of at least one 3-deoxyanthocyanidine compound of formula (1): <Desc / Clms Page number 33>  branched, saturated or not; a straight or branched chain C1 to C12 acyloxy group, saturated or unsaturated; a straight or branched chain C1 to C12 alkyl group, saturated or unsaturated; or a linear or branched, acyclic or cyclic C 2 to C 30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N = CYiY2, in which Y1 and Y2 denote, independently of one another: # a hydrogen atom; or a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C 2 to C 30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 -C 30 alkylaryl group, said group being optionally substituted with at least one substituent different from a hydrogen atom; or Y1 and Y2 together form a ring having from 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably selected from carbon, nitrogen, oxygen and sulfur, and said cycle being able to be substituted or not, aromatic or not; and (2) R6 denotes - a hydrogen atom; or <Desc / Clms Page number 34> C30, said group being optionally substituted with at least one substituent different from a hydrogen atom; or b): (1) the substituents R 1 to R 11 are defined such that at least two substituents R 1 and R 1 + 1 (x = 1 to 10) together form a ring having from 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably selected from  a halogen; or - a nitro group, a nitrile group, a radical comprising at least one atom chosen from silicon, sulfur and phosphorus atoms; or a linear or branched, acyclic or cyclic C 2 to C 30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted by at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N = CYiY2, in which Y1 and Y2 denote, independently of one another: # a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C2-C301 alkenyl group, said group optionally being interrupted by at least one heteroatom, especially a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted with minus a substituent other than a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 6 alkylaryl group <Desc / Clms Page number 35> Rx + 1 forming a ring, are as defined in (A); and (B): wherein X- represents: an anion derived from an organic acid, in particular an anion acetate, borate, citrate, tartrate, bisulfate, sulfate or phosphate; or an anion derived from a mineral acid, in particular anion bromide, chloride, borotetrafluoride or perchloride; or an anion derived from a sulfate or sulfonate group; for the preparation of a medicament for treating microbial infections in mammals, including humans.  carbon, nitrogen, oxygen and sulfur, and said cycle may be substituted or unsubstituted, aromatic or not; and (2) substituents R1 to R10 other than Rx and 2. Use according to claim 1, characterized in that said 3-deoxyanthocyanidine compound is an antimicrobial agent. 3. Use according to claim 2, characterized in that said antimicrobial agent is an antibacterial agent. 4. Use according to claim 2, characterized in that said antimicrobial agent is an antifungal agent. 5. Use of at least one 3-deoxyanthocyanidine compound of formula (I): <Desc / Clms Page number 36> C1 to C12 straight or branched chain, saturated or not; or - a nitro group; a nitrile group; a radical comprising at least one atom chosen from silicon, sulfur and phosphorus atoms; or - a -O-glycosyl group; a -O-glycosyl group substituted with at least one straight or branched chain C1-C12 alkoxy group, saturated or unsaturated; a straight or branched chain C1 to C12 acyloxy group, saturated or unsaturated; a straight or branched chain C1 to C12 alkyl group, saturated or unsaturated; or a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group being optionally interrupted C12 straight or branched chain, saturated or not; an alkyl group  wherein: (A): a): (1) R 1, R 2, R 3, R 4, R 5, R 7, R 8, R 9, R 10 and R 11 denote, independently of one another: - a hydrogen atom; or - a halogen; or - a hydroxy group; a straight or branched chain C1 to C12 alkoxy group, saturated or unsaturated, a C1 to C4 acyloxy group;

<Desc / Clms Page number 37>  by at least one heteroatom, especially a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N = CY1Y2, in which Y1 and Y2 denote, independently of one another: - a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C 2 to C 30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 -C 30 alkylaryl group, said group being optionally substituted with at least one substituent different from a hydrogen atom; or Y1 and Y2 together form a ring having from 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably selected from carbon, nitrogen, oxygen and sulfur, and said cycle being able to be substituted or not, aromatic or not; and (2) R6 denotes - a hydrogen atom; or - a halogen; or - a nitro group, a nitrile group, a radical comprising at least one atom chosen from silicon, sulfur and phosphorus atoms; or <Desc / Clms Page number 38> C30, said group being optionally substituted with at least one substituent different from a hydrogen atom; or b): (1) the substituents R 1 to R 11 are defined such that at least two substituents R 1 and R 1 + 1 (x = 1 to 10) together form a ring having from 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably selected from carbon, nitrogen, oxygen and sulfur, and said ring may be substituted or unsubstituted, aromatic or not; and  a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group optionally being interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted with minus a substituent other than a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N = CY1Y2, in which Y1 and Y2 denote, independently of one another: # a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C 2 to C 30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 6 alkylaryl group <Desc / Clms Page number 39> Rx + 1 forming a ring, are as defined in (A); and in which X represents an anion derived from an organic acid, in particular an anion acetate, borate, citrate, tartrate, bisulfate, sulfate or phosphate, or an anion derived from a mineral acid, in particular a anion bromide, chloride, borotetrafluoride or perchloride, or an anion derived from a sulphate or sulphonate group, for the preparation of a cosmetic product.  (2) the substituents R 1 to R 10 other than the substituents R 1 and 6. Use of at least one 3-deoxyanthocyanidine compound of formula (I):

 wherein: (A): a): (1) R1, R2, R3, R4, R5, R7, R8, R9, R10 and R11, independently of one another, are: <Desc / Clms Page number 40>  a hydrogen atom; or - a halogen; or - a hydroxy group; a straight or branched chain C1-C12 alkoxy group, saturated or unsaturated; a straight or branched chain C1 to C12 acyloxy group, saturated or unsaturated; a straight or branched chain C1 to C12 alkyl group, saturated or unsaturated; or - a nitro group; a nitrile group; a radical comprising at least one atom chosen from silicon, sulfur and phosphorus atoms; or - a -O-glycosyl group; a -O-glycosyl group substituted with at least one straight or branched chain C1-C12 alkoxy group, saturated or unsaturated; a straight or branched chain C 1 -C 12 acyloxy group, saturated or unsaturated; a straight or branched chain C1 to C12 alkyl group, saturated or unsaturated; or a linear or branched, acyclic or cyclic C 2 to C 30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N = CYiY2, in which Y1 and Y2 denote, independently of one another: - a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or <Desc / Clms Page number 41>  nitrogen, and / or being optionally substituted with at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 -C 30 alkylaryl group, said group being optionally substituted with at least one substituent different from a hydrogen atom; or - Y1 and Y2 together form a ring comprising from 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably chosen from carbon, nitrogen, oxygen and sulfur atoms, and said cycle being able to be substituted or not, aromatic or not; and (2) R6 denotes - a hydrogen atom; or - a halogen; or - a nitro group, a nitrile group, a radical comprising at least one atom chosen from silicon, sulfur and phosphorus atoms; or a linear or branched, acyclic or cyclic C 2 to C 30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N = CYiY2, in which Y1 and Y2 denote, independently of one another: # a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group being optionally interrupted by at least one <Desc / Clms Page number 42> Rx + 1 forming a ring, are as defined in (A); and in which X represents an anion derived from an organic acid, in particular an anion acetate, borate, citrate, tartrate, bisulfate, sulfate or phosphate, or an anion derived from a mineral acid, in particular a anion bromide, chloride, borotetrafluoride or perchloride, or anion derived from a sulphate or sulphonate group for the control of microbial diseases in plants. C30, said group being optionally substituted with at least one substituent different from a hydrogen atom; or b): (1) the substituents R1 to R11 are defined such that at least two substituents Rx and Rx + 1 (x = 1 to 10) together form a ring having from 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably selected from carbon, nitrogen, oxygen and sulfur, and said ring may be substituted or unsubstituted, aromatic or not; and (2) the substituents R 1 to R 10 other than the substituents R x and  a heteroatom, especially a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted with at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 6 alkylaryl group 7. Use of at least one 3-deoxyanthocyanidine compound of formula (I): <Desc / Clms Page number 43> C1 to C12 straight or branched chain, saturated or not; or - a nitro group; a nitrile group; a radical comprising at least one atom chosen from silicon, sulfur and phosphorus atoms; or - a -O-glycosyl group; a -O-glycosyl group substituted with at least one straight or branched chain C1-C12 alkoxy group, saturated or unsaturated; a straight or branched chain C1 to C12 acyloxy group, saturated or unsaturated; a straight or branched chain C1 to C12 alkyl group, saturated or unsaturated; or a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group being optionally interrupted C12 straight or branched chain, saturated or not; an alkyl group  wherein: (A): a): (1) R 1, R 2, R 3, R 4, R 5, R 7, R 8, R 8, R 10 and R 11 denote, independently of one another: - a hydrogen atom; or - a halogen; or - a hydroxy group; a straight or branched chain C1-C12 alkoxy group, saturated or unsaturated; a C1 to C acyloxy group

<Desc / Clms Page number 44>  by at least one heteroatom, especially a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N = CY1Y2, in which Y1 and Y2 denote, independently of one another: # a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C 2 to C 30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 -C 30 alkylaryl group, said group being optionally substituted with at least one substituent different from a hydrogen atom; or Y1 and Y2 together form a ring having from 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably selected from carbon, nitrogen, oxygen and sulfur, and said cycle being able to be substituted or not, aromatic or not; and (2) R6 denotes - a hydrogen atom; or - a halogen; or - a nitro group, a nitrile group, a radical comprising at least one atom chosen from silicon, sulfur and phosphorus atoms; or <Desc / Clms Page number 45> C30, said group being optionally substituted with at least one substituent different from a hydrogen atom; or b): (1) the substituents R1 to R11 are defined such that at least two substituents Rx and Rx + 1 (x = 1 to 10) together form a ring having from 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably selected from carbon, nitrogen, oxygen and sulfur, and said ring may be substituted or unsubstituted, aromatic or not; and  a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group optionally being interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted with minus a substituent other than a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N = CYiY2 in which Y1 and Y2 denote, independently of one another: # a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C 2 to C 30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 6 alkylaryl group <Desc / Clms Page number 46> Rx + 1 forming a ring, are as defined in (A); and (B): wherein X- represents: an anion derived from an organic acid, in particular an anion acetate, borate, citrate, tartrate, bisulfate, sulfate or phosphate; or an anion derived from a mineral acid, in particular anion bromide, chloride, borotetrafluoride or perchloride; or an anion derived from a sulfate or sulfonate group; for the preservation of products, preferably food, perishable.  (2) the substituents R 1 to R 10 other than the substituents R 1 and 8. Use of at least one 3-deoxyanthocyanidine compound of formula (I):

 in which: (A): a): (1) R 1, R 2, R 3, R 4, R 5, R 7, R 8, R 9, R 10 and R 11 denote, independently of one another: <Desc / Clms Page number 47>  a hydrogen atom; or - a halogen; or - a hydroxy group; a straight or branched chain C1-C12 alkoxy group, saturated or unsaturated; a straight or branched chain C1 to C12 acyloxy group, saturated or unsaturated; a straight or branched chain C1 to C12 alkyl group, saturated or unsaturated; or - a nitro group; a nitrile group; a radical comprising at least one atom chosen from silicon, sulfur and phosphorus atoms; or - a -O-glycosyl group; a -O-glycosyl group substituted with at least one straight or branched chain C1-C12 alkoxy group, saturated or unsaturated; a straight or branched chain C1 to C12 acyloxy group, saturated or unsaturated; a straight or branched chain C1 to C12 alkyl group, saturated or unsaturated; or a linear or branched, acyclic or cyclic C 2 to C 30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - a group -NYiY2 or N = CYiY2, in which Y1 and Y2 denote, independently of each other: # a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a C 2 to C 30 alkenyl group, linear or branched, acyclic or cyclic, said group being optionally interrupted by at least one heteroatom, especially a heteroatom of oxygen, sulfur or <Desc / Clms Page number 48>  nitrogen, and / or being optionally substituted with at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or Y1 and Y2 together form a ring having from 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably selected from carbon, nitrogen, oxygen and sulfur, and said cycle being able to be substituted or not, aromatic or not; and (2) R6 denotes - a hydrogen atom; or - a halogen; or - a nitro group, a nitrile group, a radical comprising at least one atom chosen from silicon, sulfur and phosphorus atoms; or a linear or branched, acyclic or cyclic C 2 to C 30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N = CY1Y2, in which Y1 and Y2 denote, independently of one another: # a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group being optionally interrupted by at least one <Desc / Clms Page number 49> Rx + 1 forming a ring, are as defined in (A); and (B): wherein X- represents: an anion derived from an organic acid, in particular an anion acetate, borate, citrate, tartrate, bisulfate, sulfate or phosphate; or an anion derived from a mineral acid, in particular anion bromide, chloride, borotetrafluoride or perchloride; or an anion derived from a sulfate or sulfonate group; for the preparation of antimicrobial materials. C30, said group being optionally substituted with at least one substituent different from a hydrogen atom; or b): (1) the substituents R 1 to R 11 are defined such that at least two substituents R 1 and R 1 + 1 (x = 1 to 10) together form a ring having from 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably selected from carbon, nitrogen, oxygen and sulfur, and said ring may be substituted or unsubstituted, aromatic or not; and (2) the substituents R 1 to R 10 other than the substituents R x and  a heteroatom, especially a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted with at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 6 alkylaryl group 9. 3-Deoxyanthocyanidine compound of formula (II): <Desc / Clms Page number 50> C12 straight or branched chain, saturated or not; or - a nitro group; a nitrile group; or a radical comprising at least one atom chosen from silicon, sulfur and phosphorus atoms; or - a -O-glycosyl group; a -O-glycosyl group substituted with at least one straight or branched chain C1-C12 alkoxy group, saturated or unsaturated; a straight or branched chain C1 to C12 acyloxy group, saturated or unsaturated; a straight or branched chain C1 to C12 alkyl group, saturated or unsaturated; or  wherein: (A): the substituents: a): (1) R1, R2, R4, R5, R7, R8, R9 and R11 denote, independently of one another: - a hydrogen atom; or - a halogen; or - a hydroxy group; a straight or branched chain C1-C12 alkoxy group, saturated or unsaturated; a straight or branched chain C1 to C12 acyloxy group, saturated or unsaturated; a C1 to C4 alkyl group

<Desc / Clms Page number 51>  a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group optionally being interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one a substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N = CYiY2, in which Y1 and Y2 denote, independently of one another: # a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted with minus a substituent other than a hydrogen atom; or an aryl group, an aralkyl group or a C6 to C30 alkylaryl group, said group being optionally substituted by at least one substituent different from a hydrogen atom, or - Y1 and Y2 together form a ring comprising From 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably selected from carbon, nitrogen, oxygen and sulfur, and said ring may be substituted or unsubstituted, aromatic or not; and (2) R3, R6, R10 denote, independently of one another: - a hydrogen atom; or - a halogen; or <Desc / Clms Page number 52>  a nitro group; a nitrile group; a radical comprising at least one atom chosen from an atom of silicon, sulfur and phosphorus; or a linear or branched, acyclic or cyclic C 2 to C 30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted by at least one substituent different from a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or - a group -NY1Y2 or N = CYiY2, in which Y1 and Y2 denote, independently of one another: # a hydrogen atom; or # a straight or branched, saturated or unsaturated C 1 -C 12 alkyl group; or a linear or branched, acyclic or cyclic C2 to C30 alkenyl group, said group being optionally interrupted by at least one heteroatom, in particular a heteroatom of oxygen, sulfur or nitrogen, and / or being optionally substituted with minus a substituent other than a hydrogen atom; or an aryl group, an aralkyl group or a C 6 to C 30 alkylaryl group, said group being optionally substituted with at least one substituent other than a hydrogen atom; or b): (1) the substituents R1 to R11 are defined such that at least two substituents Rx and Rx + 1 (x = 1 to 10) together form a ring having from 4 to 8 atoms, preferably from 5 to 7 atoms, said atoms being preferably selected from <Desc / Clms Page number 53> Rx + 1 forming a ring, are as defined in (A); and (B): wherein X- represents: - an anion derived from an organic acid, in particular an anion acetate, borate, citrate, tartrate, bisulfate, sulfate or phosphate; or an anion derived from a mineral acid, in particular anion bromide, chloride, borotetrafluoride or perchloride; or an anion derived from a sulphate or sulphonate group.  carbon, nitrogen, oxygen and sulfur, and said cycle may be substituted or unsubstituted, aromatic or not; and (2) substituents R1 to R10 other than Rx and 10. A compound according to claim 9 as a medicament. 11. Process for the preparation of a compound according to claim 9 or 10, in which the substituent R7 is a hydrogen atom, said process comprising at least: the condensation in an acid medium of an acetophenone (compound A) with an orthohydroxybenzaldehyde (compound B), according to the following reaction:

<Desc / Clms Page number 54>  A process for the preparation of a compound according to claim 9 or 10, wherein the substituent R 7 is not a hydrogen atom, said process comprising at least: the acidic condensation of a 1-phen-1 3-dione (compound A) with a phenol (compound B), according to the following reaction: